Seriously, who else remembers having a 486 running Windows 3.1 on DOS 6.22 and having boot menus allowing the machine to boot with the settings necessary to play different games? Many configurations because every freaking game was different.
This one should be posted by the support guy at the game company, dealing with me, when I was just a (l)user back then. I bought a game for my 386 with a 10 MB HDD. The game required over 15 MB of space. I ran doublespace, but still wasn't able to install the game. I actually called the company to complain. To the rep's credit, he didn't laugh in my face, but patiently explained how compression worked.
My more spectacular fail was trying to use DOS 5 version of Laplink to connect a laptop. My system had a 25-pin "serial" port, but it was the wrong gender. You all see where this is going, right? I bought a gender bender at Radio Shack, and proceeded to blow up my motherboard!